Katekoli

Katekoli
Tunnisteet
IUPAC-nimi 1,2-dihydroksibentseeni
CAS-numero 120-80-9
PubChem CID 289
Ominaisuudet
Molekyylikaava C6H6O2
Moolimassa 110,11 g/mol
Ulkomuoto Värittömiä kiteitä
Sulamispiste 105 °C (378 K)
Kiehumispiste 245,5 °C (519 K)
Tiheys 1,34 g/cm3
Liukoisuus veteen veteen 43 g/100 ml

Katekoli on orgaaninen yhdiste (fenoli) muodostuen bentseenirenkaasta ja siihen liittyneestä kahdesta hydroksyyliryhmästä (OH). Katekoli on huoneenlämmössä (20 °C) olomuodoltaan kiinteää, värittömiä kiteitä, joilla on tunnusomainen haju. Kiteet muuttuvat ruskeiksi ilman tai valon vaikutuksesta. Sen kemiallinen kaava on C6H6O2 ja rakennekaava on C6H4(OH)2. Katekolista käytetään myös nimityksiä pyrokatekoli, 1,2-bentseenidioli, ja 1,2-dihydroksibentseeni. Katekoli on bentseenidiolin isomeerinen muoto resorsinolin (1,3-bentseenidioli) ja hydrokinonin (1,4-bentseenidioli) kanssa.

Katekolin moolimassa on 110,11 g/mol, sulamispiste 105 °C, kiehumispiste 245,5 °C, suhteellinen tiheys 1,344 g/cm3 (vesi = 1,0 g/cm3), leimahduspiste 127 °C (c.c.), itsesyttymislämpötila 510 °C sekä CAS-numero 120-80-9. Katekolia liukenee veteen 43 g/100 ml.

Ympäristö- ja terveysvaikutukset

Lyhytaikainen altistus ärsyttää ihoa, hengitys- ja ruoansulatusteitä sekä syövyttää silmiä. Aineelle altistumisesta voi seurata vaikutuksia keskushermostossa, johtaen keskushermoston toiminnan heikkenemiseen, kouristuksiin ja hengitysvajeeseen. Altistuminen voi aiheuttaa verenpaineen nousua. Toistuva tai pitkäaikainen ihokosketus voi aiheuttaa ihon herkistymisen.

Valmistus ja käyttö

Varhaisimmat katekolin valmistusmenetelmät perustuivat kivihiilitervan tislaukseen tai 2-kloorifenolin hydrolyysiin, mutta nämä menetelmät ovat nykyään vain vähän käytettyjä. Katekolia voidaan valmistaa fenolin ja vetyperoksidin välisellä reaktiolla, eliminaatioreaktiolla 1,2-syklohekseenidiolista tai kuumentamalla pfenoli-sulfonihappoa emäksen kuten kaliumhydroksidin läsnä ollessa. Katekolia käytetään hapetuksenestoaineena ja valokuvien kehityksessä reagenssina. Tärkeimmät käyttökohteet ovat kuitenkin muiden yhdisteiden, kuten guajakolin, väriaineiden ja maatalouskemikaalien karbofuraanin ja propoksuurin valmistaminen.[1][2][3]

Lähteet

  1. Alén, Raimo: Kokoelma orgaanisia yhdisteitä: Ominaisuudet ja käyttökohteet, s. 190. Helsinki: Consalen Consulting, 2009. ISBN 978-952-92-5627-3
  2. Léon Krumenacker, Michael Constantini, P. Pontal & J. Sentenac: Hydroquinone, Resorcinol, and Catechol, Kirk-Othmer Encyclopedia of Chemical Technology, John Wiley & Sons, New York, 2000. Viitattu 20.04.2013
  3. Helmut Fiege, Heinz-Werner Voges, Toshikazu Hamamoto, Sumio Umemura, Tadao Iwata, Hisaya Miki, Yasuhiro Fujita, Hans-Josef Buysch, Dorothea Garbe& Wilfried Paulus: Phenol Derivatives, Ullmann's Encyclopedia of Industrial Chemistry, John Wiley & Sons, New York, 2000. Viitattu 20.04.2013

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